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BACKGROUND: Surgery residency confers stress burdens on trainees. To monitor and mitigate areas of concerns, our education team implemented a 6-item biannual survey querying potential stressors. We reviewed the initial 5-year experience to assess for trends and improve efforts in maintaining resident well-being. STUDY DESIGN: Surgery residents from all postgraduate years were asked to complete a survey of common concerns, prioritizing them in order of importance. The items to be ranked were: needs of family/friends; nonwork time for study; financial concerns; personal well-being needs; concerns for clinical performance; and administrative demands. Changes in ranking were trended across 10 review periods. Results were analyzed using a Kruskal–Wallis test. RESULTS: A completion rate of 96.5% was rendered from the completion of 333 surveys. Rankings changed significantly for nonwork time for study (p = 0.04), personal well-being needs (p = 0.03) and concerns for clinical performance (p = 0.004). Nonwork time for study and concerns on clinical performance were consistently ranked as top two stressors over study period, except for spring 2020. Personal well-being needs ranked highest in spring 2020; 41% of residents placed this as top 2 rankings. A decrease in concerns for clinical performance was observed in spring 2020, corresponding to the coronavirus disease 2019 (COVID-19) pandemic emergency declaration. CONCLUSIONs: Surgery residents generally prioritized time for study and concerns for assessment of clinical performance as highest areas of concern. With the occurrence of a pandemic, increased prioritization of personal well-being was observed. Used routinely with biannual reviews, the survey was able to identify plausible changes in resident concerns. Determination of levels of actual stress and actual association with the pandemic requires additional study.